Synthesis of 2,5-Diaryl-1,5-dienes from Allylic Bromides Using Visible-Light Photoredox Catalysis

Pratsch, Gerald; Overman, Larry E.

doi:10.1021/acs.joc.5b01962

Cited by 19 publications

(18 citation statements)

References 74 publications

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“…The title compound was concentrated to produce a colorless oil (2.24 g, 94% yield). 1 H NMR (500 MHz, CDCl3): δ 7.36 (dt, J = 7.1, 3.1 Hz, 5H), 7.30 -7.25 (m, 2H), 7.17 (d, J = 7.9 Hz, 2H), 5 hex-1-en-2-ylbenzene (S35) was prepared on a 5.28 mmol scale according to a published literature procedure. 2 The title compound was isolated using automated column chromatography eluting with Hexanes (10 CV).…”

Section: -Methyl-4-(1-phenylvinyl)benzene (S34)mentioning

confidence: 99%

Direct Use of Carboxylic Acids in the Photocatalytic Hydroacylation of Styrenes To Generate Dialkyl Ketones

et al. 2019

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I. General Information Materials. Commercial reagents were acquired from Sigma-Aldrich, Alfa Aesar, Acros, Strem, TCI, or Oakwood and used as received. Diethyl ether (Et2O), tetrahydrofuran (THF), and toluene (PhMe) were dried by passing through activated alumina columns and stored over molecular sieves in a N2-filled glovebox; N,N-dimethylformamide (DMF) was dried by passing through a column of activated molecular sieves. Acetonitrile (MeCN) was purchased from Millipore Sigma without sieves and subsequently sparged with nitrogen before bringing it into the glovebox. Sieves were detrimental for reactivity. Instrumentation. Proton nuclear magnetic resonance (1 H NMR) spectra were recorded on a Bruker 500 AVANCE spectrometer (500 MHz), a Bruker NB 300 spectrometer (300 MHz), or a Bruker Avance III HD NanoBay (400 MHz) spectrometer. Deuterium nuclear magnetic resonance (2 H NMR) spectra were recorded on a Bruker 500 AVANCE spectrometer (77 MHz). Carbon nuclear magnetic resonance (13 C NMR) spectra were recorded on a Bruker 500 AVANCE spectrometer (126 MHz). Fluorine nuclear magnetic resonance (19 F NMR) spectra were recorded on a Bruker NB 300 spectrometer (282 MHz). Chemical shifts for protons are reported in parts per million (ppm) downfield from tetramethylsilane and are referenced to residual protium in the NMR solvent (CHCl3 =  7.26 ppm). Chemical shifts for carbon are reported in parts per million downfield from tetramethylsilane and are referenced to the carbon resonances of the solvent residual peak (CDCl3 =  77.16 ppm). Chemical shifts for fluorine are reported in parts per million referenced to CFCl3 ( 0 ppm). NMR data are represented as follows: chemical shift ( ppm), multiplicity (s = singlet, bs = broad singlet, d = doublet, appd = apparent doublet, t = triplet, q = quartet, p = pentet, sx = sextet m = multiplet), coupling constant in Hertz (Hz), integration. Reversed-phase liquid chromatography/mass spectrometry (LC/MS) was performed on an Agilent 1260 Infinity analytical LC and Agilent 6120 Quadrupole LC/MS system, using electrospray ionization/atmospheric-pressure chemical ionization (ESI/APCI), and UV detection at 254 and 280 nm. High-resolution mass spectra were obtained on an Agilent 6220 LC/MS using electrospray ionization time-of-flight (ESI-TOF) or Agilent 7200 gas chromatography/mass spectrometry using electron impact time-of-flight (EI-TOF). Gas chromatography was performed on an Agilent 7890A series instrument equipped with a split-mode capillary injection system and flame ionization detectors. Fourier transform infrared (FT-IR) spectra were recorded on a Perkin-Elmer Spectrum 100 and are reported in terms of frequency of absorption (cm-1). High-performance liquid chromatography (HPLC) was performed on an Agilent 1200 series instrument with a binary pump and a diode array detector, using Chiralcel OD-H (25 cm x 0.46 cm), Chiralcel OJ-H (25 cm x 0.46 cm), Chiralpak ASH (25 cm x 0.46 cm), Chiralpak AD-H (25 cm x 0.46 cm), Chiralpak IC (25 cm x 0.46 cm) and Chiralpack ID (25 cm x 0.46 cm). ...

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Section: -Methyl-4-(1-phenylvinyl)benzene (S34)mentioning

confidence: 99%

Direct Use of Carboxylic Acids in the Photocatalytic Hydroacylation of Styrenes To Generate Dialkyl Ketones

et al. 2019

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“…The titled compound was prepared in 89% yield (1.216 g, 9.20 mmol) according to the similar procedure mentioned in 1-methyl-4-(propen-2-yl)benzene with methyltriphenylphosphonium iodide (4.853 g, 12.0 mmol), 1.55 M n -butyllithium in n -hexane (8.00 mL, 12.4 mmol), and 3′-methylacetophenone (1.382 g, 10.3 mmol) for 17 h as a colorless oil: 1 H NMR (CDCl 3 , 400 MHz): δ 2.14 (dd, J = 0.8 and 1.4 Hz, 3H), 2.36 (s, 3H), 5.06 (quint, J = 1.5 Hz, 1H), 5.34–5.35 (m, 1H), 7.09 (d, J = 7.7 Hz, 1H), 7.22 (t, J = 7.3 Hz, 1H), 7.27 (d, J = 7.5 Hz, 1H), 7.28 (s, 1H). 21…”

Section: Methodsmentioning

confidence: 99%

“…: 22 33.5–34.5 °C], 1 H NMR (CDCl 3 , 300 MHz): δ 2.13 (s, 3H), 3.82 (s, 3H), 4.99 (quint, J = 1.5 Hz, 1H), 5.29 (m, 1H), 6.86 (diffused d, J = 8.9 Hz, 2H), 7.42 (diffused d, J = 9.0 Hz, 2H). 21…”

Section: Methodsmentioning

confidence: 99%

Selective Formation of Internal Olefinic Trimer of α-Methylstyrenes with HI Gas and Ketones

et al. 2018

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Reaction of α-methylstyrene in the presence of HI gas and methyl p -tolyl ketone selectively resulted in an internal olefinic trimer. We revealed that the ketones with the stabilization of the protonated state were efficient to give the corresponding trimers, whereas the other ketones gave the usual indane compound. From the investigation for the mechanistic path, we found that the trimer is a kinetic product and that indane is a thermodynamic product.

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“…2015 年, Gong 课题组 [20] 报道了叔卤代烷烃与 Ar-X 偶联, 通过添加二甲氨基吡啶(DMAP)(或吡啶) 并且保证整个催化循环的进行. 除此之外, 采用电化学方法 [21] 或者光催化方法 [22]…”

Section: 图式 5 卤代芳烃与卤代烯烃偶联 Scheme 5 Cross Coupling Of Aryl Halides Witunclassified

Recent Advance in Ni-Catalyzed Reductive Cross-Coupling to Construct C(sp²)-C(sp²) and C(sp²)-C(sp³) Bonds

李娅琼¹,

范玉航²,

贾乾发³

2019

Chin. J. Org. Chem.

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镍催化还原偶联反应构筑 C(sp 2)-C(sp 2)/C(sp 2)-C(sp 3)键的研究进展李娅琼范玉航贾乾发 * (长江师范学院化学化工学院重庆 408100) 摘要亲电试剂的还原偶联反应避免了有机金属试剂的制备与使用, 对各类官能团拥有极好的兼容性, 为 CC 键的构筑提供了一类重要的方法. 近些年来, 该反应的研究取得了突破性进展, 实现了一系列 C(sp 2)-X 与 C(sp 3)-X 亲电试剂参与的交叉偶联反应. 主要针对镍催化亲电试剂交叉偶联反应构筑 C(sp 2)-C(sp 2)和 C(sp 2)-C(sp 3)键的研究展开综述, 详细介绍了各种偶联反应及其反应机制.

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Synthesis of 2,5-Diaryl-1,5-dienes from Allylic Bromides Using Visible-Light Photoredox Catalysis

Cited by 19 publications

References 74 publications

Direct Use of Carboxylic Acids in the Photocatalytic Hydroacylation of Styrenes To Generate Dialkyl Ketones

Direct Use of Carboxylic Acids in the Photocatalytic Hydroacylation of Styrenes To Generate Dialkyl Ketones

Selective Formation of Internal Olefinic Trimer of α-Methylstyrenes with HI Gas and Ketones

Recent Advance in Ni-Catalyzed Reductive Cross-Coupling to Construct C(sp²)-C(sp²) and C(sp²)-C(sp³) Bonds

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Synthesis of 2,5-Diaryl-1,5-dienes from Allylic Bromides Using Visible-Light Photoredox Catalysis

Cited by 19 publications

References 74 publications

Direct Use of Carboxylic Acids in the Photocatalytic Hydroacylation of Styrenes To Generate Dialkyl Ketones

Direct Use of Carboxylic Acids in the Photocatalytic Hydroacylation of Styrenes To Generate Dialkyl Ketones

Selective Formation of Internal Olefinic Trimer of α-Methylstyrenes with HI Gas and Ketones

Recent Advance in Ni-Catalyzed Reductive Cross-Coupling to Construct C(sp2)-C(sp2) and C(sp2)-C(sp3) Bonds

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Product

Resources

About

Recent Advance in Ni-Catalyzed Reductive Cross-Coupling to Construct C(sp²)-C(sp²) and C(sp²)-C(sp³) Bonds